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Hydrotrifluoromethylthiolation of Unactivated Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride through Deoxygenative Reduction and Photoredox Radical Processes
Author(s) -
Ouyang Yao,
Xu XiuHua,
Qing FengLing
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201911323
Subject(s) - chemistry , reagent , photoredox catalysis , catalysis , photochemistry , radical initiator , medicinal chemistry , organic chemistry , photocatalysis , copolymer , polymer
An ongoing challenge in trifluoromethylthiolation reactions is the use of less expensive and easily available trifluoromethylthio sources. Herein, we disclose an unprecedented usage of trifluoromethanesulfonic anhydride (Tf 2 O) as a radical trifluoromethylthiolating reagent. Hydrotrifluoromethylthiolation of unactivated alkenes and alkynes with Tf 2 O in the presence of PMePh 2 and H 2 O under visible‐light photoredox catalysis gave the addition products. The trifluoromethylthio radical ( . SCF 3 ) was first formed from Tf 2 O through a photoredox radical processes and deoxygenative reduction of PMePh 2 , and H 2 O serves as the H‐atom donor for the hydrotrifluoromethylthiolation reaction. This reaction provides a new strategy for radical trifluoromethylthiolation.